Summer Weekend on Cape Ann, Massachusetts | Weekend Away

As I write this from the confines of self-quarantine, Cape Ann feels impossibly distant, though it’s less than 40 miles from where I sit. I call up memories of sunny summer afternoons and find the effort both a stretch and a salve. Perhaps by the time you read this, beach days will once again be possible.

Whatever this stay-at-home era may bring, we at least have this certainty: The joy of travel is also in the anticipation. So let’s savor this moment of armchair wandering. And when the day finally comes to leave home and get back on the road, here’s what I’ll do: I’ll take my family to Good Harbor Beach in Gloucester and park at the very back of the lot, where a trail leads to a tidal river that rises and falls with the Atlantic. There, we’ll read and body surf until we’re tired, and then we’ll drive over to the Lobster Pool in Rockport to eat fried fish sandwiches and watch the sun drop into Ipswich Bay. Before heading home, we’ll stop for penny candy at Tuck’s.

Summer Weekend on Cape Ann, Massachusetts | Gloucester & Rockport

FRIDAY

Settle in and order up.

The 2016 opening of the Beauport Hotel,anelegant 94-room establishment overlooking Pavilion Beach, was a watershed moment in Gloucester’s reemergence as a resort town. Shingled and gambrel-roofed, it resembles New England’s grand old seaside hotels, and it stands in a neighborhood known as The Fort, which has long been the center of the fishing industry (the hotel’s rooftop pool, which offers full bar service, is named after the Birdseye plant that once stood here). While there are active commercial fishing docks behind the hotel, it is oriented toward the sea, with a stunning view of Ten Pound Island and the summer cottages along the southwestern shore. Rooms are done in a modern nautical style, and the restaurant serves a nice buffet brunch on the large terrace. 

A more intimate though equally stylish option is the Addison Choate Hotel, whose seven rooms have all been recently redone. It’s just a stone’s throw from some of Rockport’s main attractions: Bearskin Neck (more on that later) and the iconic fish shack Motif No. 1.

Ready for dinner? Short & Main has been a foodie magnet in downtown Gloucester since opening in 2013. Owners Nico Monday and Amelia O’Reilly met while working at the famed Chez Panisse and bring a Cali-fresh sensibility to the menu. Try the long-fermented, wood-fired pizzas (the sausage-rapini pie is terrific), the excellent crudo and other local seafood, and the seasonal salads that put local produce in the spotlight.

SATURDAY

Eat, stroll, repeat.

Follow the locals toSugar Magnolia’sin downtown Gloucester, where the pineapple fritters, breakfast sammies, and loaded pancakes (carrot cake, banana-walnut) will start you off right.  

Feeling a bit too full afterward? A perfect antidote is the docent-led walking tour by the Cape Ann Museum that follows in the footsteps of artists like Edward Hopper, Fitz Henry Lane, and Winslow Homer. Circle back to the museum to admire its collection of contemporary works, bold-name artists, and stunning depictions of Gloucester’s fishing heyday in photographs, paintings, and artifacts.

Close by the museum, Virgilio’s Bakery & Deli brings a Little Italy vibe to downtown Gloucester. Pick up a sub (try the North Ender: prosciutto, fresh mozzarella, sun-dried tomatoes, basil) and a cannoli or a flaky sfogliatelle pastry, which could match that of any North End bakery. Stop in for a book at the Bookstore of Gloucester, a top-notch indie, then stroll a few blocks for a picnic in the garden oasis of the Sargent House Museum, a 1782 Georgian home that once belonged to Judith Sargent Murray, a writer and early women’s rights activist (some works by her descendant John Singer Sargent are on display inside). If you could access the attic here, you’d see across the rooftops and the harbor all the way to Eastern Point, your next stop, which is a short drive away.

Soak up culture and commerce.

The peninsula of Eastern Point has maintained an air of exclusivity since the 19th century, when one family owned it all and forbade public access. There’s still a guard at the entrance, but this seems mostly ceremonial, since everyone is invited to tour Beauport, the Sleeper-McCann House,operated by Historic New England. In a region rich in historic homes, this could be considered the crown jewel: a 40-room waterfront mansion designed by Henry Sleeper, the celebrity decorator of his day. He conceived of Beauport as a series of showrooms, each done in a different style, from early colonial to Arts and Crafts to chinoiserie. It’s like entering a life-size dollhouse, a portal to a more glamorous era. No wonder Isabella Stewart Gardner was a frequent guest.

For an afternoon of wandering, Cape Ann offers two artsy-boutiquey neighborhoods: Bearskin Neck in Rockport and Rocky Neck in Gloucester. Both are worthy options, but with dinner in mind you may want to focus on the Bearskin, which is stuffed with boutiques, galleries, ice cream shops, and tourist bric-a-brac. Of note: Joe’s Fresh Fish Prints, where owner Joe Higgins practices the Japanese art of gyotaku, and Lula’s Pantry, a home goods store with a coastal vibe. For a quick snack, check out Helmut’s Strudel, an Austrian pastry shop.

Enjoy a little night music.

If you’re lucky enough to have tickets for a concert at Rockport’s stunning Shalin Liu Performance Center,with its floor-to-ceiling water-view window behind the stage, opt for an early (or late) dinner at Feather & Wedge, named after tools used to cut Rockport’s famous granite. It’s a small, chic sanctuary for seasonal fare. Sit at the bar for the local scene, or go for a table to better focus on that summer pea salad and locally made pasta with lobster and corn. Just be sure to reserve ahead.

SUNDAY

Reach the beach.

Grab breakfast pastries and lunch sandwiches at Sandpiper Bakery, maker of croissants, seasonal scones, and ham and Brie on homemade focaccia.

Public beach parking lots fill up early but start to slowly empty out after 2 p.m., so plan accordingly. The best public-access beaches are Good Harbor and Wingaersheek,which both have parking and amenities, stunning views, and soft white sand. Good Harbor’s best feature is the comparatively warm water of the river that borders the southern end and carries lazy rafters down its final run to the sea. On the ocean side, waves here are more dramatic, but families with young kids love the river at low tide. Meanwhile, Wingaersheek has a long, shallow bay filled with smooth rocks that are perfect for climbing. At low tide, the shallow water goes on forever, ideal for wading and gazing out to Annisquam Light in the distance.

Let the sun go down on you.

Honestly, the food at the Lobster Pool is only half the draw. This ramshackle restaurant offers solid fish-shack fare; it’s the kind of place where it’s OK to show up with sandy feet. But what makes it a must-visit is its location on Folly Cove, with a sweeping view of Ipswich Bay. This is the northwest corner of the cape, and if you time it right and sit on the lawn, you’ll enjoy your lobster dinner and onion rings in the rosy light of a spectacular sunset. Regulars bring their own wine and watch the spectacle together, cheering as the last flare sinks into the deep. A perfect finale to a perfect weekend.